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Compound Detail

CHEMBL204593

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Cc1cc(S(=O)(=O)N[C@@H](C(=O)NO)C2CCOCC2)ccc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL204593
Phase Preclinical
Structure Type MOL
InChI Key LUCFRFDOOYLALP-CYBMUJFWSA-N
8
Targets
12
Activities
2
Assay Types
30
PK Parameters
19
Publications
0
Known Names

Molecular Properties

346.4
MW (Da)
0.71
ALogP
5
HBA
3
HBD
104.7
PSA (Ų)
0.54
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H19FN2O5S
MW 346.38
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness -1.46

Activity Summary

IC50 10 meas. best 7.27
Ki 2 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lethal factor
CHEMBL4372
 Ki 7.62 7.62 24.0 2
Lethal factor
CHEMBL4372
 IC50 7.27 7.0733 54.0 3
Stromelysin-1
CHEMBL283
 IC50 5.85 5.85 1400.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 5.7 5.7 2000.0 1
72 kDa type IV collagenase
CHEMBL333
 IC50 5.7 5.7 2000.0 1
Interstitial collagenase
CHEMBL332
 IC50 5.66 5.66 2200.0 1
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 5.37 5.37 4300.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 5.19 5.19 6500.0 1
Neprilysin
CHEMBL1944
 IC50 5.03 5.03 9400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 72.0 mL.min-1.kg-1 Mus musculus
CL 80.0 mL.min-1.kg-1 Rattus norvegicus
CL 24.0 mL.min-1.kg-1 Cavia porcellus
CL 14.0 mL.min-1.kg-1 Oryctolagus cuniculus
CL 35.0 mL.min-1.kg-1 Oryctolagus cuniculus
CL 15.0 mL.min-1.kg-1 Canis lupus familiaris
CL 23.0 mL.min-1.kg-1 Macaca mulatta
Cmax 120.0 nM Mus musculus
Cmax 240.0 nM Rattus norvegicus
Cmax 250.0 nM Cavia porcellus
Cmax 12.0 nM Oryctolagus cuniculus
Cmax 730.0 nM Canis lupus familiaris
Cmax 120.0 nM Macaca mulatta
F 20.0 % Mus musculus
F - % Mus musculus
F 51.0 % Rattus norvegicus
F 71.0 % Rattus norvegicus
F 22.0 % Cavia porcellus
F - % Cavia porcellus
F - % Oryctolagus cuniculus
F 0.5 % Oryctolagus cuniculus
F 57.0 % Canis lupus familiaris
F - % Canis lupus familiaris
F - % Macaca mulatta
F 16.0 % Macaca mulatta
T1/2 0.4 hr Mus musculus
T1/2 1.4 hr Rattus norvegicus
T1/2 1.2 hr Cavia porcellus
T1/2 2.0 hr Oryctolagus cuniculus
T1/2 2.5 hr Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lethal factor Ki = 24.0 nM 7.62 Competitive inhibition of Bacillus anthracis recombinant lethal factor expressed... 24290062
Lethal factor Ki = 24.0 nM 7.62 Binding affinity to Bacillus anthracis lethal factor assessed as inhibition cons... 34624823
Lethal factor IC50 = 54.0 nM 7.27 Inhibition of LF by FRET assay 16338135
Lethal factor IC50 = 54.0 nM 7.27 Inhibition of LF 16338135
Lethal factor IC50 = 210.0 nM 6.68 Inhibition of LF by MACK assay 16338135
Stromelysin-1 IC50 = 1400.0 nM 5.85 Inhibition of MMP3 16338135
72 kDa type IV collagenase IC50 = 2000.0 nM 5.7 Inhibition of MMP2 16338135
Matrix metalloproteinase-9 IC50 = 2000.0 nM 5.7 Inhibition of MMP9 16338135
Interstitial collagenase IC50 = 2200.0 nM 5.66 Inhibition of MMP1 16338135
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 4300.0 nM 5.37 Inhibition of TACE 16338135
Matrix metalloproteinase-14 IC50 = 6500.0 nM 5.19 Inhibition of MMP14 16338135
Neprilysin IC50 = 9400.0 nM 5.03 Inhibition of NEP 16338135

Literature References

PubMed DOI Target Context # Activities
16338135 10.1016/j.bmcl.2005.10.088 Oryctolagus cuniculus 10
16338135 10.1016/j.bmcl.2005.10.088 Rhesus monkey 7
16338135 10.1016/j.bmcl.2005.10.088 Canis familiaris 7
16338135 10.1016/j.bmcl.2005.10.088 Cavia porcellus 7
16338135 10.1016/j.bmcl.2005.10.088 Rattus norvegicus 7
16338135 10.1016/j.bmcl.2005.10.088 Mus musculus 7
16338135 10.1016/j.bmcl.2005.10.088 Lethal factor 3
16338135 10.1016/j.bmcl.2005.10.088 Matrix metalloproteinase-14 1
34624823 10.1016/j.ejmech.2021.113877 Lethal factor 1
24290062 10.1016/j.bmc.2013.11.009 Lethal factor 1
16338135 10.1016/j.bmcl.2005.10.088 No relevant target 1
16338135 10.1016/j.bmcl.2005.10.088 Matrix metalloproteinase-9 1
16338135 10.1016/j.bmcl.2005.10.088 Stromelysin-1 1
16338135 10.1016/j.bmcl.2005.10.088 72 kDa type IV collagenase 1
16338135 10.1016/j.bmcl.2005.10.088 Interstitial collagenase 1
16338135 10.1016/j.bmcl.2005.10.088 Disintegrin and metalloproteinase domain-containing protein 17 1
16338135 10.1016/j.bmcl.2005.10.088 Neprilysin 1
16338135 10.1016/j.bmcl.2005.10.088 Endothelin-converting enzyme 1 1
16338135 10.1016/j.bmcl.2005.10.088 Angiotensin-converting enzyme 1

Data from ChEMBL 36 via Core Engine